In vitro and in vivo effects of the conformationally restricted polyamine analogue CGC-11047 on small cell and non-small cell lung cancer cells (original) (raw)

• Abeloff MD, Slavik M, Luk GD, Griffin CA, Hermann J, Blanc O, Sjoerdsma A, Baylin SB (1984) Phase I trial and pharmacokinetic studies of alpha-difluoromethylornithine—an inhibitor of polyamine biosynthesis. J Clin Oncol 2:124–130
  PubMed CAS Google Scholar
• Abeloff MD, Rosen ST, Luk GD, Baylin SB, Zeltzman M, Sjoerdsma A (1986) Phase ii trials of alpha-difluoromethylornithine, an inhibitor of polyamine synthesis, in advanced small cell lung cancer and colon cancer. Cancer Treat Rep 70:843–845
  PubMed CAS Google Scholar
• Babbar N, Casero RA Jr (2006) Tumor necrosis factor-alpha increases reactive oxygen species by inducing spermine oxidase in human lung epithelial cells: a potential mechanism for inflammation-induced carcinogenesis. Cancer Res 66:11125–11130
  Article PubMed CAS Google Scholar
• Bergeron RJ, McManis JS, Liu CZ, Feng Y, Weimar WR, Luchetta GR, Wu Q, Ortiz-Ocasio J, Vinson JR, Kramer D et al (1994) Antiproliferative properties of polyamine analogues: A structure-activity study. J Med Chem 37:3464–3476
  Article PubMed CAS Google Scholar
• Bergeron RJ, Feng Y, Weimar WR, McManis JS, Dimova H, Porter C, Raisler B, Phanstiel O (1997) A comparison of structure-activity relationships between spermidine and spermine analogue antineoplastics. J Med Chem 40:1475–1494
  Article PubMed CAS Google Scholar
• Bernacki RJ, Bergeron RJ, Porter CW (1992) Antitumor activity of N,N’-bis(ethyl)spermine homologues against human malme-3 melanoma xenografts. Cancer Res 52:2424–2430
  PubMed CAS Google Scholar
• Bernacki RJ, Oberman EJ, Seweryniak KE, Atwood A, Bergeron RJ, Porter CW (1995) Preclinical antitumor efficacy of the polyamine analogue N1, N11- diethylnorspermine administered by multiple injection or continuous infusion. Clin Cancer Res 1:847–857
  PubMed CAS Google Scholar
• Boncher T, Bi X, Varghese S, Casero RA Jr, Woster PM (2007) Polyamine-based analogues as biochemical probes and potential therapeutics. Biochem Soc Trans 35:356–363
  Article PubMed CAS Google Scholar
• Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254
  Article PubMed CAS Google Scholar
• Casero RA, Frydman B, Murray Stewart T, Woster PA (2005) Significance of targeting polyamine metabolism as an antineoplastic strategy: unique targets for polyamine analogues. West Pharm Soc 289:C826–835
  Google Scholar
• Casero RA Jr, Celano P, Ervin SJ, Porter CW, Bergeron RJ, Libby PR (1989) Differential induction of spermidine/spermine N1-acetyltransferase in human lung cancer cells by the bis(ethyl)polyamine analogues. Cancer Res 49:3829–3833
  PubMed CAS Google Scholar
• Casero RA Jr, Ervin SJ, Celano P, Baylin SB, Bergeron RJ (1989) Differential response to treatment with the bis(ethyl)polyamine analogues between human small cell lung carcinoma and undifferentiated large cell lung carcinoma in culture. Cancer Res 49:639–643
  PubMed CAS Google Scholar
• Casero RA Jr, Celano P, Ervin SJ, Wiest L, Pegg AE (1990) High specific induction of spermidine/spermine N1-acetyltransferase in a human large cell lung carcinoma. Biochem J 270:615–620
  PubMed CAS Google Scholar
• Casero RA Jr, Celano P, Ervin SJ, Applegren NB, Wiest L, Pegg AE (1991) Isolation and characterization of a cdna clone that codes for human spermidine/spermine N1-acetyltransferase. J Biol Chem 266:810–814
  PubMed CAS Google Scholar
• Casero RA Jr, Mank AR, Xiao L, Smith J, Bergeron RJ, Celano P (1992) Steady-state messenger RNA and activity correlates with sensitivity to N1,N12-bis(ethyl)spermine in human cell lines representing the major forms of lung cancer. Cancer Res 52:5359–5363
  PubMed CAS Google Scholar
• Casero RA Jr, Pegg AE (1993) Spermidine/spermine N1-acetyltransferase—the turning point in polyamine metabolism. Faseb J 7:653–661
  PubMed CAS Google Scholar
• Casero RA Jr, Gabrielson EW, Pegg AE (1994) Immunohistochemical staining of human spermidine/spermine N1-acetyltransferase superinduced in response to treatment with antitumor polyamine analogues. Cancer Res 54:3955–3958
  PubMed CAS Google Scholar
• Casero RA Jr, Woster PM (2001) Terminally alkylated polyamine analogues as chemotherapeutic agents. J Med Chem 44:1–26
  Article PubMed CAS Google Scholar
• Casero RA Jr, Wang Y, Stewart TM, Devereux W, Hacker A, Smith R, Woster PM (2003) The role of polyamine catabolism in anti-tumour drug response. Biochem Soc Trans 31:361–365
  Article PubMed CAS Google Scholar
• Casero RA Jr, Marton LJ (2007) Targeting polyamine metabolism and function in cancer and other hyperproliferative diseases. Nat Rev Drug Discov 6:373–390
  Article PubMed CAS Google Scholar
• Chang BK, Bergeron RJ, Porter CW, Liang Y (1992) Antitumor effects of n-alkylated polyamine analogues in human pancreatic adenocarcinoma models. Cancer Chemother Pharmacol 30:179–182
  Article PubMed CAS Google Scholar
• Chang BK, Bergeron RJ, Porter CW, Vinson JR, Liang Y, Libby PR (1992) Regulatory and antiproliferative effects of N-alkylated polyamine analogues in human and hamster pancreatic adenocarcinoma cell lines. Cancer Chemother Pharmacol 30:183–188
  Article PubMed CAS Google Scholar
• Chen Y, Kramer DL, Diegelman P, Vujcic S, Porter CW (2001) Apoptotic signaling in polyamine analogue-treated SK-MEL-28 human melanoma cells. Cancer Res 61:6437–6444
  PubMed CAS Google Scholar
• Creaven PJ, Perez R, Pendyala L, Meropol NJ, Loewen G, Levine E, Berghorn E, Raghavan D (1997) Unusual central nervous system toxicity in a phase I study of N1,N11 diethylnorspermine in patients with advanced malignancy. Invest New Drugs 15:227–234
  Article PubMed CAS Google Scholar
• Devereux W, Wang Y, Stewart TM, Hacker A, Smith R, Frydman B, Valasinas AL, Reddy VK, Marton LJ, Ward TD et al (2003) Induction of the PAOh1/SMO polyamine oxidase by polyamine analogues in human lung carcinoma cells Cancer. Chemother Pharmacol 52:383–390
  Article CAS Google Scholar
• Frydman B, Porter CW, Maxuitenko Y, Sarkar A, Bhattacharya S, Valasinas A, Reddy VK, Kisiel N, Marton LJ, Basu HS (2003) A novel polyamine analog (SL-11093) inhibits growth of human prostate tumor xenografts in nude mice. Cancer Chemother Pharmacol 51:488–492
  PubMed CAS Google Scholar
• Gabrielson E, Tully E, Hacker A, Pegg AE, Davidson NE, Casero RA Jr (2004) Induction of spermidine/spermine N1-acetyltransferase in breast cancer tissues treated with the polyamine analogue N1, N11-diethylnorspermine. Cancer Chemother Pharmacol 54:122–126
  Article PubMed CAS Google Scholar
• Gerner EW, Meyskens FL Jr (2004) Polyamines and cancer: old molecules, new understanding. Nat Rev Cancer 4:781–792
  Article PubMed CAS Google Scholar
• Ha HC, Woster PM, Yager JD, Casero RA Jr (1997) The role of polyamine catabolism in polyamine analogue-induced programmed cell death. Proc Natl Acad Sci USA 94:11557–11562
  Article PubMed CAS Google Scholar
• Hahm HA, Ettinger DS, Bowling K, Hoker B, Chen TL, Zabelina Y, Casero RA Jr (2002) Phase I study of N1,N11-diethylnorspermine in patients with non-small cell lung cancer. Clin Cancer Res 8:684–690
  PubMed CAS Google Scholar
• Huang Y, Hager ER, Phillips DL, Dunn VR, Hacker A, Frydman B, Kink JA, Valasinas AL, Reddy VK, Marton LJ et al (2003) A novel polyamine analog inhibits growth and induces apoptosis in human breast cancer cells. Clin Cancer Res 9:2769–2777
  PubMed CAS Google Scholar
• Kabra PM, Lee HK, Lubich WP, Marton LJ (1986) Solid-phase extraction and determination of dansyl derivatives of unconjugated and acetylated polyamines by reversed-phase liquid chromatography: improved separation systems for polyamines in cerebrospinal fluid, urine and tissue. J Chromatogr 380:19–32
  Article PubMed CAS Google Scholar
• Levin VA, Hess KR, Choucair A, Flynn PJ, Jaeckle KA, Kyritsis AP, Yung WK, Prados MD, Bruner JM, Ictech S et al (2003) Phase iii randomized study of postradiotherapy chemotherapy with combination alpha-difluoromethylornithine-pcv versus pcv for anaplastic gliomas. Clin Cancer Res 9:981–990
  PubMed CAS Google Scholar
• Marton LJ, Pegg AE (1995) Polyamines as targets for therapeutic intervention. Annu Rev Pharmacol Toxicol 35:55–91
  Article PubMed CAS Google Scholar
• McCloskey DE, Casero RA Jr, Woster PM, Davidson NE (1995) Induction of programmed cell death in human breast cancer cells by an unsymmetrically alkylated polyamine analogue. Cancer Res 55:3233–3236
  PubMed CAS Google Scholar
• Mitchell JL, Simkus CL, Thane TK, Tokarz P, Bonar MM, Frydman B, Valasinas AL, Reddy VK, Marton LJ (2004) Antizyme induction mediates feedback limitation of the incorporation of specific polyamine analogues in tissue culture. Biochem J 384:271–279
  Article PubMed CAS Google Scholar
• Mitchell JL, Thane TK, Sequeira JM, Marton LJ, Thokala R (2007) Antizyme and antizyme inhibitor activities influence cellular responses to polyamine analogs. Amino Acids 33:291–297
  Article PubMed CAS Google Scholar
• Pless M, Belhadj K, Menssen HD, Kern W, Coiffier B, Wolf J, Herrmann R, Thiel E, Bootle D, Sklenar I et al (2004) Clinical efficacy, tolerability, and safety of SAM486a, a novel polyamine biosynthesis inhibitor, in patients with relapsed or refractory non-Hodgkin’s lymphoma: results from a phase II multicenter study. Clin Cancer Res 10:1299–1305
  Article PubMed CAS Google Scholar
• Porter CW, Sufrin JR (1986) Interference with polyamine biosynthesis and/or function by analogs of polyamines or methionine as a potential anticancer chemotherapeutic strategy. Anticancer Res 6:525–542
  PubMed CAS Google Scholar
• Porter CW, Bergeron RJ (1988) Enzyme regulation as an approach to interference with polyamine biosynthesis—an alternative to enzyme inhibition. Adv Enzyme Regul 27:57–79
  Article PubMed CAS Google Scholar
• Porter CW, Ganis B, Libby PR, Bergeron RJ (1991) Correlations between polyamine analogue-induced increases in spermidine/spermine N1-acetyltransferase activity, polyamine pool depletion, and growth inhibition in human melanoma cell lines. Cancer Res 51:3715–3720
  PubMed CAS Google Scholar
• Porter CW, Bernacki RJ, Miller J, Bergeron RJ (1993) Antitumor activity of N1,N11-bis(ethyl)norspermine against human melanoma xenografts and possible biochemical correlates of drug action. Cancer Res 53:581–586
  PubMed CAS Google Scholar
• Reddy VK, Valasinas A, Sarkar A, Basu HS, Marton LJ, Frydman B (1998) Conformationally restricted analogues of N1,N11-bisethylspermine: synthesis and growth inhibitory effects on human tumor cell lines. J Med Chem 41:4723–4732
  Article PubMed CAS Google Scholar
• Reddy VK, Sarkar A, Valasinas A, Marton LJ, Basu HS, Frydman B (2001) Cis-unsaturated analogues of 3,8,13,18,23-pentaazapentacosane (BE-4-4-4-4): synthesis and growth inhibitory effects on human prostate cancer cell lines. J Med Chem 44:404–417
  Article PubMed CAS Google Scholar
• Seely JE, Pegg AE (1983) Ornithine decarboxylase (mouse kidney). Methods Enzymol 94:158–161
  Article PubMed CAS Google Scholar
• Seiler N (2003) Thirty years of polyamine-related approaches to cancer therapy. Retrospect and prospect. Part 2. Structural analogues and derivatives. Curr Drug Targets 4:565–585
  Article PubMed CAS Google Scholar
• Seiler N (2003) Thirty years of polyamine-related approaches to cancer therapy. Retrospect and prospect. Part 1. Selective enzyme inhibitors. Curr Drug Targets 4:537–564
  Article PubMed CAS Google Scholar
• Streiff RR, Bender JF (2001) Phase I study of N1-N11-diethylnorspermine (denspm) administered tid for 6 days in patients with advanced malignancies. Invest New Drugs 19:29–39
  Article PubMed CAS Google Scholar
• Valasinas A, Sarkar A, Reddy VK, Marton LJ, Basu HS, Frydman B (2001) Conformationally restricted analogues of N1,N14-bisethylhomospermine (BE-4-4-4): synthesis and growth inhibitory effects on human prostate cancer cells. J Med Chem 44:390–403
  Article PubMed CAS Google Scholar
• Wallace HM, Fraser AV (2003) Polyamine analogues as anticancer drugs. Biochem Soc Trans 31:393–396
  Article PubMed CAS Google Scholar
• Wallace HM, Fraser AV (2004) Inhibitors of polyamine metabolism: review article. Amino Acids 26:353–365
  Article PubMed CAS Google Scholar
• Wang Y, Devereux W, Woster PM, Stewart TM, Hacker A, Casero RA Jr (2001) Cloning and characterization of a human polyamine oxidase that is inducible by polyamine analogue exposure. Cancer Res 61:5370–5373
  PubMed CAS Google Scholar
• Wang Y, Murray-Stewart T, Devereux W, Hacker A, Frydman B, Woster PM, Casero RA Jr (2003) Properties of purified recombinant human polyamine oxidase, PAOh1/SMO. Biochem Biophys Res Commun 304:605–611
  Article PubMed CAS Google Scholar
• Wang Y, Casero RA (2006) Mammalian polyamine catabolism: a therapeutic target, a pathological problem, or both? J Biochem 139:17–25
  Article PubMed CAS Google Scholar
• Waters WR, Frydman B, Marton LJ, Valasinas A, Reddy VK, Harp JA, Wannemuehler MJ, Yarlett N (2000) [N1,N12]bis(ethyl)-cis-6,7-dehydrospermine: A new drug for treatment and prevention of cryptosporidium parvum infection of mice deficient in t-cell receptor alpha. Antimicrob Agents Chemother 44:2891–2894
  Article PubMed CAS Google Scholar
• Wolff AC, Armstrong DK, Fetting JH, Carducci MK, Riley CD, Bender JF, Casero RA Jr, Davidson NE (2003) A phase ii study of the polyamine analog N1,N11-diethylnorspermine (DENSpm) daily for five days every 21 days in patients with previously treated metastatic breast cancer. Clin Cancer Res 9:5922–5928
  PubMed CAS Google Scholar